Process for the preparation of aliphatic sulphoacids



Patented Aug. 22, 1933 UNITED STATES PATENT OFFICE PROCESS FOR THEPREPARATION OF ALI- PHATIC SULPHOACIDS Heinrich Bertsch, Chemnitz,Germany assignor to H. Th. Biihme Aktiengesellschaft, Chemnitz, Germany,a Corporation of Germany No Drawing. Application October 10,

Serial 311,713, and in Germany October 11,

3 Claims.

This invention relates to the preparation of aliphatic sulpho-acidssuitable for textile purposes, particularly as wetting, cleaning andemulsifying agents. 1 a

It is known that higher fatty acids of the oleic or ricinoleic acid typepartly enter into addition compounds with sulphuric acid and partly formsulphuric acid esters when treated with sulphuric acid. These additioncompounds or'esters have 1 long been known and used under the name ofTurkey red oils in the form of their sodium salts. As may be explainedfrom their chemical constitution, they are substances of comparativelylittle stability and consequently decompose, on

"' boiling with water or dilute acids; back into products, the sulphuricment with sulphuric acid in the presence oforganic acid anhydrides oracid chlorides and that the resultant reaction products diifer in afundamental fashion from the highterto known, so-called sulphonatedoils. The action of the sulphuric acid, is clearly no longer upon thedouble linkage or on the hydroxyl group with the efiect that an additionor esterification takes place, but it is to be assumed that a hydrogenatom in the methylene group adjacent the double linkage is replaced bythe sulpho-acid radicle 40 and that a genuine aliphatic sulpho-acid isthus produced which can no longer be claimed to be or regarded as aTurkey red oil. This assumption is based upon the fact that such analiphatic sulpho-acid does not split off a sulphuric acid radicle eitheron boiling with water or on boiling with acids or even on treatment withalkalies and that consequently it exhibits complete resistance to allsaponifying agencies. Thus, it behaves absolutely analogously to anaromatic sul- 'ph'o-acid so that there can no longer be any question ofan addition compound or a sulphuric acid ester. This class of substancesso produced, and

not hitherto used in the textile industry has extremely valuableproperties which make it particularly suitable for use' in the entiretextile and leather industries. It forms, for example, -readily solublealkali, or alkaline earth and magnesium salts and is thus thoroughlyresistant to the action of hard water. For wetting, cleaning,emulsifying or like purposes it may be used mixed with hydrocarbons orhalo-hydrocarbons.

, Example I 300 'kgs. of oleic acid are mixed with 100 kgs. of aceticanhydride and brought into reaction with 300 kgs. of sulphuric acid attemperatures below 10. After the mixture has become clearly soluble inwater, the excess presence of sulphuric acid is washed outwith Glaubersalt solution. The resultant sulpho-acid is clearly soluble in water.The sulpho-acid may be used as such or in the form of. the sodium saftobtained by neutralization. The alkali salts may also be prepared in adry form and even in this condition retain their valuablecharacteristics.

Example '11 100 kgs. of linoleic acid methyl ester are treated with 39kgs. of acetyl chloride and sulphonated at 0 with 100 kgs. of sulphuricacid. After washing, a sulpho-acid of properties equally valuable withthose in Example I is obtained.

The following Formula: I and II indicate the reactions which in allprobability take place concurrently and Formula III indicates thereactions in which the sulfurizing is efiected without the addition oforganic acid derivatives.

' soul coon+2 011.0001:

CH: (Cl 12h CH=CH CH (CHzh COOH-t-Z HQSOl-I- (CHaCO)zO=CH3 (CH:) GHQ-CHCH (CH1);

00011 2 0H, coon III.

- Q0311 ice I claim: 1. Process for the preparation of aliphaticsulpho-acids distinguished by. the treatment of rated aliphaticoxy-compounds with sulphuric acid in the presence of not considerablymore than one molecular weight of an anhydrous organic acid radicalcompound per one double linkage of fatty acid molecule.

2. Process for the preparation of an aliphatic sulpho-acid'distinguishedby the treatment of an unsaturated aliphatic acid of higher molecularweight with the exception of oxy-fatty acids with sulphuric acid in thepresence or not consider-

